Cyclophanes. 10. Synthesis and conformational behavior of [2.2](2,5)pyrrolophanes

Haley, J.; Rosenfeld, Stuart M.; Keehn, Philip M.

doi:10.1021/jo00428a025

Cited by 20 publications

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“…The intrinsic structural features of [2 n ]cyclophanes make them attractive probes to investigate and to comprehend the interplay between strain versus aromaticity, the role of transannular effects ( through-bond and through-space interactions), − the effects of substituents in transannular π–π interactions, , chemical shifts in aromatic systems, intramolecular charge transfer processes, − and transannular reactions . Cyclophanes have also been employed as selective catalysts, as auxiliaries in asymmetric synthesis, as catalysts that simulate enzymatic functions, in supramolecular chemistry, in optoelectronic devices, , as precursors of nonlinear optical materials, and in the preparation of artificial receptors. , The occurrence of transannular interactions , in cyclophanes has been detected not only by photoelectrons spectroscopy and by electronic spin resonance (ESR) , but also by other spectroscopic analyses such UV–vis and NMR .…”

Section: Introductionmentioning

confidence: 99%

Ruthenophanes: Evaluating Cation−π Interactions in [Ru(η⁶-C₁₆H₁₂R₄)(NH₃)₃]^2+/3+ Complexes. A Computational Insight

et al. 2014

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The nature of cation−π interactions in a set of [Ru(η6-C16H12R4)(NH3)3]2+3+ (R = F, CN, CH3, and others), complexes was investigated with Su–Li energy decomposition analysis and the natural orbitals for chemical valence and the extended transition state method EDA-NOCV. The long-distance effects of electron-donating and electron-withdrawing substituents as well as protonation of the ipso carbon on the nature of cation−π interactions were investigated. Both energy decomposition analyses, Su–Li EDA and EDA-NOCV, are in total agreement, showing that the presence of electron-donating substituents such as CH3, NH2, and H3CO tends to stabilize the ruthenium–arene interaction while electron-withdrawing substituents such as F, CN, and NO2 tend to weaken such interactions. The electrostatic component of the ruthenium–arene interaction is the most affected by the substitution, despite the fact that the covalent character is much more significant than the electrostatic character. EDA-NOCV reveals that the most important orbital stabilization comes from donation and back-donation between the interacting fragments, while the σ density deformations present a moderate contribution to total orbital stabilization energy in ruthenium–arene interactions of complexes 1–8.

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Section: Introductionmentioning

confidence: 99%

Ruthenophanes: Evaluating Cation−π Interactions in [Ru(η⁶-C₁₆H₁₂R₄)(NH₃)₃]^2+/3+ Complexes. A Computational Insight

et al. 2014

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Darstellung von Imidazolo‐ und Pyrrolophanen durch [3+2]‐Cycloadditionen mit Azaallenyl‐Radikalkationen

Müller

Mattay

1992

Angewandte Chemie

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Dibenzodiazapyracylenes: Doubly N‐Doped Cyclopenta‐Fused Polycyclic Molecules That Exhibit High Carrier Mobility

et al. 2022

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Pyracylene is a unique cyclopenta-fused polycyclic aromatic hydrocarbon (CP-PAH) that exhibits dual aromatic characteristics. Herein we report the synthesis of doubly N-doped benzannulated pyracylenes, namely dibenzodiazapyracylenes, by oxidative NÀ N linking reaction of [2.2](2,5)pyrrolophane-type precursors. Dibenzodiazapyracylenes displayed well-ordered πstacked molecular packing in the solid state, which were feasible for effective hole-transporting along the stacking direction. High carrier mobility was estimated by microwave conductivity measurements as compared to dibenzoullazine. The high HOMO level of dibenzodiazapyracylene was verified by electrochemistry and its persistent radical cation species has been detected.

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Cyclophanes. 10. Synthesis and conformational behavior of [2.2](2,5)pyrrolophanes

Cited by 20 publications

References 3 publications

Ruthenophanes: Evaluating Cation−π Interactions in [Ru(η⁶-C₁₆H₁₂R₄)(NH₃)₃]^2+/3+ Complexes. A Computational Insight

Ruthenophanes: Evaluating Cation−π Interactions in [Ru(η⁶-C₁₆H₁₂R₄)(NH₃)₃]^2+/3+ Complexes. A Computational Insight

Darstellung von Imidazolo‐ und Pyrrolophanen durch [3+2]‐Cycloadditionen mit Azaallenyl‐Radikalkationen

Dibenzodiazapyracylenes: Doubly N‐Doped Cyclopenta‐Fused Polycyclic Molecules That Exhibit High Carrier Mobility

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Cyclophanes. 10. Synthesis and conformational behavior of [2.2](2,5)pyrrolophanes

Cited by 20 publications

References 3 publications

Ruthenophanes: Evaluating Cation−π Interactions in [Ru(η6-C16H12R4)(NH3)3]2+/3+ Complexes. A Computational Insight

Ruthenophanes: Evaluating Cation−π Interactions in [Ru(η6-C16H12R4)(NH3)3]2+/3+ Complexes. A Computational Insight

Darstellung von Imidazolo‐ und Pyrrolophanen durch [3+2]‐Cycloadditionen mit Azaallenyl‐Radikalkationen

Dibenzodiazapyracylenes: Doubly N‐Doped Cyclopenta‐Fused Polycyclic Molecules That Exhibit High Carrier Mobility

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Ruthenophanes: Evaluating Cation−π Interactions in [Ru(η⁶-C₁₆H₁₂R₄)(NH₃)₃]^2+/3+ Complexes. A Computational Insight

Ruthenophanes: Evaluating Cation−π Interactions in [Ru(η⁶-C₁₆H₁₂R₄)(NH₃)₃]^2+/3+ Complexes. A Computational Insight